Stop Overthinking Small Decisions

“I was hoping you could help me with something I’ve been struggling with for a few weeks,” it began.

The email was more than 400 words long, and laid out his thoughtful consideration of three possible solutions for a decision he was having trouble with.

The decision?

What kind of publications should he reach out to for guest blogging relationships?

It’s not a trivial decision, of course. Whichever path he chooses will result in a different outcome.

But the truth is, he could have answered that question for himself in just a few days of action, rather than struggling with it for weeks of indecision.

I replied with a story that I’ve shared before, but that I’d like to share again today, because it’s an important remind for all of us (myself included).

This isn’t a post written to discourage asking for advice. Far from it; I love getting questions from entrepreneurs.

Nor is it a post to discourage thoughtfulness.

It’s a post about just how dangerous being too thoughtful⁠—about the wrong things⁠—can be.

I’ve Made This Mistake

“Stop.”

Taken aback, I asked him what he meant.

“Just stop. Seriously. Make a call and move on. This isn’t that important.”

Not that important?! This is our domain we’re talking about. Our entire identity!

“You’ve been waffling on this for weeks. Pick something and get back to work. I know it doesn’t seem that way now, but you can always change your mind, and the cost of doing it later will be minimal compared to the cost of staying distracted now.”

My advisor was right.

We had been going back on forth on which domain to host our site on—Groovehq.com versus a half-dozen other alternatives—and we weren’t getting anywhere.

And more importantly, it was a daily distraction.

An easy problem to deliberate on instead of doing the hard work of building a product, talking to our audience, validating our assumptions and getting into the market.

He was right, and I should’ve listened sooner. Finally, we gave in and decided to go with groovehq.com.

Developing a Preference forAction Over Analysis

Coming to terms with the fact that Habla was not going to work for them as they moved forward, the team made a long list of names whose .com domains were available.

One of those names was Olark.

Tired of the back-and-forth debate on names, Ben finally put his foot down.

“Eventually I said, hey guys, let’s just be Olark for the next week. It’s short, it’s easy to spell, it doesn’t have any connotation and we can really own the brand. Let’s just see what it feels like for a week.”

People in businesses all over the world, every single day, spend far too long making decisions big and small.

It’s especially true, however, in startups, where we’re building things from the ground up. With the feeling of ownership that comes with, we feel a need to get every little piece “perfect.”

Unfortunately, that hurts us badly.

And it’s a lesson that I didn’t learn the first time that it hurt me. Or the fifth. Or maybe even the fiftieth.

There’s a certain cadence that you can feel when you spend time hanging any well-run startup company. The management team has to have a bias toward making decisions. They know that a 70% accurate decision made quickly and based on sound principles is better than a 90% decision made after careful consideration.

The startup entrepreneur knows that they’re going to be wrong often. They’re flexible and willing to admit when they’re wrong. They don’t create a culture of punishment for mistakes. They live be the credo that if you’re never making mistakes you’re not trying hard enough.

In my mind the sign of a great entrepreneur is the one that spots the 30% scenario quickly and adjusts but doesn’t get gun shy about rapid decision-making in the future.

In fact, analysis paralysis drives me fucking bonkers. It is not uncommon in a meeting for me to say, “There are three choices: A, B, C. My gut tells me that we ought to do B. But let’s decide as a group. I don’t care if my view isn’t selected. Let’s make a decision and move on.”

Mark Suster

Mark’s advice is spot on and any entrepreneur would do well to heed it.

But it took me some time.

When Over-Analyzing Decisions Hurts the Most

I think that the most visible and relatable example for most entrepreneurs here has to do with firing team members.

It’s hard to fire somebody. Nobody wants to, or enjoys doing it.

But on small teams, bad players can be toxic. Whether they’re simply not pulling their weight, or something far more insidious (like ego) is at play, a weak link degrades the whole chain.

A founder friend said something to me a while ago that made it crystal clear why I had been slow to fire in the past: because it was a reflection on me: